Carbon-carbon formation via Ni-catalyzed Suzuki-Miyaura coupling through C-CN bond cleavage of aryl nitrile.
نویسندگان
چکیده
The Suzuki-Miyaura coupling of aryl nitriles with aryl/alkenyl boronic esters is reported. With this method, the cyano group could be applied as a protecting group of arenes and finally as a leaving group to further construct polyaryl scaffolds.
منابع مشابه
Suzuki-Miyaura cross-coupling reaction catalyzed using highly efficient CN-dimeric ortho-palladated complex under microwave irradiation and conventional heating
Suzuki cross-coupling reaction of different aryl halides with arylboronic acids was successfully carried out in methanol using ortho-palladated complex of 2-methoxyphenethylamine. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of this complex as efficient and active catalyst. Application of microwave irradiation improved the yields of th...
متن کاملSuzuki-Miyaura cross-coupling reaction catalyzed using highly efficient CN-dimeric ortho-palladated complex under microwave irradiation and conventional heating
Suzuki cross-coupling reaction of different aryl halides with arylboronic acids was successfully carried out in methanol using ortho-palladated complex of 2-methoxyphenethylamine. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of this complex as efficient and active catalyst. Application of microwave irradiation improved the yields of th...
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The nickel(0) fragment [(dippe)Ni] has been found to react with a variety of aromatic nitriles. Initial pi-coordination to the C=C and Ctbd1;N bonds of 2-cyanoquinoline is found to lead ultimately to C-CN oxidative addition. 3-Cyanoquinoline reacts similarly, although no eta(2)-CN complex is observed. 2-, 3-, And 4-cyanopyridines react initially to give eta(2)-nitrile complexes that then lead t...
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Halogenated quinazolinones and quinazolines are versatile synthetic intermediates for the metal-catalyzed carbon-carbon bond formation reactions such as the Kumada, Stille, Negishi, Sonogashira, Suzuki-Miyaura and Heck cross-coupling reactions or carbon-heteroatom bond formation via the Buchwald-Hartwig cross-coupling to yield novel polysubstituted derivatives. This review presents an overview ...
متن کاملSuzuki-Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C-N and C-O bonds.
The Suzuki-Miyaura cross-coupling has been widely recognized as one of the most important methods for the construction of C-C bonds. However, in contrast to traditional aryl halide or pseudohalide electrophiles, coupling reactions with unactivated C-N and C-O electrophiles have proven significantly more challenging. Here we report the first general palladium-catalyzed Suzuki-Miyaura cross-coupl...
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ورودعنوان ژورنال:
- Organic letters
دوره 11 15 شماره
صفحات -
تاریخ انتشار 2009